My plans

Prestige is everything in painting portraits. As of right now I have just a small amount of prestige but not enough to do this as a living. Of course it is my goal to increase my status. I have three pieces I am planning to do right now and they all will be done for free. That means I won't really be able to make money on this for about 2 to three months as each one should take at least a month to complete. The first is a picture of an 11 year old boy. I need to have a child's portrait in my portfolio. The next is of a judge. I figured someone in judge's robes would be an impressive looking picture. Plus I can get some press coverage for that. The third is of a mayor. That is some prestige. None of these are really the big "in" for me though. They will establish a portfolio for me though in which I can advertise and get my business started. I am doing these all for free in a sense. In other words, I am doing them for free but will take donations if they wish to give them.
Now this is all great but it still isn't the great break I need. However, I may have found that yesterday. I have a friend who is running for US Congress. He is a Republican in a strongly Republican district. He is unopposed in his primary. Therefore he stands a good chance of winning. I just got an email back from him yesterday in which he would allow me to paint his portrait should he win. This is the "in" that I am looking for. To begin with, it will strengthen me in my native home town and will allow me to advertise there. Also it will allow me to advertise in the Washington DC area. That, to me, is where I really expect the money to be.